2-(4-Chlorophenyl)ethane-1-sulfonyl chloride → 2-[2-(4-Chloro-phenyl)-ethanesulfonylamino]-5-methoxy-benzenesulfonamide

HRID 2283272Notes

Reaction equation

HRID 2283272 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[S:10]([NH2:13])(=[O:12])=[O:11].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][S:23](Cl)(=[O:25])=[O:24])=[CH:17][CH:16]=1>N1C=CC=CC=1>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][S:23]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=2[S:10]([NH2:13])(=[O:11])=[O:12])(=[O:25])=[O:24])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 27577802-(4-Chlorophenyl)ethane-1-sulfonyl chlorideHCID 112526652-Amino-5-methoxybenzenesulfonamide

Product 1

HCID 687849462-[2-(4-Chloro-phenyl)-ethanesulfonylamino]-5-methoxy-benzenesulfonamideYield 88.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-5-methoxy-benzenesulfonamide (4.0 g, 19.80 mmol) in pyridine (60 mL), 2-(4-chloro-phenyl)-ethanesulfonyl chloride (4.73 g, 19.79 mmol) was added slowly at 0° C. The reaction mixture was stirred at RT for 16 h and then concentrated under reduced pressure at 35° C. The residue was then partitioned between ethyl acetate and 1N HCl. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash column chromatography using ethyl acetate/hexane (1:1) to give the title compound (7.1 g, 88%).

Workup

  1. concentrationconcentrated under reduced pressure at 35° C
  2. customThe residue was then partitioned between ethyl acetate and 1N HCl
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-f31523dc0a204f9f99de28f9596ef87a
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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